Water → HCID 12016348, compound

HRID 2297709Notes

Reaction equation

HRID 2297709 reaction equation
[O:1]([CH2:9][CH2:10][N:11]([CH2:24][CH2:25][O:26][CH3:27])[C:12](=[O:23])[NH:13][C@@H:14]([CH3:22])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:1][CH2:9][CH2:10][N:11]([CH2:24][CH2:25][O:26][CH3:27])[C:12](=[O:23])[NH:13][C@@H:14]([CH3:22])[C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 12016347HCID 12016347, compound

Product 1

HCID 12016348HCID 12016348, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butyl (2S)-2-[3-[2-(t-butyldimethylsiloxy)ethyl]-3-(2-methoxyethyl)ureido]propionate (Compound No. 3-1, 2.79 g) is dissolved in anhydrous tetrahydrofuran (11 ml) under a nitrogen atmosphere. Tetra-n-butylammonium fluoride (7.3 ml) is added to the solution at room temperature with stirring, and the mixture is stirred for one hour. Water is added to the reaction mixture, and the whole is extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 2.14 g (quantitatively) of the titled compound (Compound No. 4-1).

Workup

  1. stirringthe mixture is stirred for one hour
  2. extractionthe whole is extracted with ethyl acetate
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b123136b09c94bdf9992bdd1fb1c8538
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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